IL109395A

IL109395A - The history of the heterocycles, the processes for their preparation and the pharmaceutical preparations containing them

The history of the heterocycles, the processes for their preparation and the pharmaceutical preparations containing them

Info

Publication number: IL109395A
Authority: IL; Israel
Prior art keywords: alkenoyl; alkyl; arylcarbamoyl; heterocyclic; amino acid
Prior art date: 1993-04-28

Application number

IL10939594A

Other languages

English (en)

Hebrew (he)

Other versions

IL109395A0 (en

Original Assignee

Fujisawa Pharmaceutical Co

Priority date

1993-04-28

Filing date

1994-04-22

Publication date

1998-09-24

1993-04-28 Priority claimed from GB939308804A external-priority patent/GB9308804D0/en

1993-09-13 Priority claimed from GB939318929A external-priority patent/GB9318929D0/en

1994-04-22 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1994-07-31 Publication of IL109395A0 publication Critical patent/IL109395A0/xx

1998-09-24 Publication of IL109395A publication Critical patent/IL109395A/en

Links

125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 102
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
238000002360 preparation method Methods 0.000 title abstract description 95
238000000034 method Methods 0.000 title abstract description 19
-1 nitro, amino Chemical group 0.000 claims abstract description 1632
125000000217 alkyl group Chemical group 0.000 claims abstract description 254
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 148
150000001875 compounds Chemical class 0.000 claims abstract description 108
125000003545 alkoxy group Chemical group 0.000 claims abstract description 86
150000003839 salts Chemical class 0.000 claims abstract description 58
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 52
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
239000001257 hydrogen Substances 0.000 claims abstract description 45
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 40
125000001424 substituent group Chemical group 0.000 claims abstract description 30
229910052736 halogen Inorganic materials 0.000 claims abstract description 29
150000002367 halogens Chemical class 0.000 claims abstract description 29
125000002252 acyl group Chemical group 0.000 claims abstract description 28
125000003118 aryl group Chemical group 0.000 claims abstract description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 12
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
125000000539 amino acid group Chemical group 0.000 claims description 445
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 157
125000001589 carboacyl group Chemical group 0.000 claims description 97
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 53
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 40
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 35
125000005843 halogen group Chemical group 0.000 claims description 19
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000003435 aroyl group Chemical group 0.000 claims description 8
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 8
125000005236 alkanoylamino group Chemical group 0.000 claims description 7
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 7
101800004538 Bradykinin Proteins 0.000 claims description 6
QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 claims description 6
102100035792 Kininogen-1 Human genes 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 claims description 6
241000282320 Panthera leo Species 0.000 claims description 5
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
125000004450 alkenylene group Chemical group 0.000 claims description 4
125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 4
125000000676 alkoxyimino group Chemical group 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000005116 aryl carbamoyl group Chemical group 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 abstract description 3
101150041968 CDC13 gene Proteins 0.000 description 242
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 242
OKKJLVBELUTLKV-MZCSYVLQSA-N CD3OD Substances [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 134
239000000203 mixture Substances 0.000 description 119
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 99
239000000243 solution Substances 0.000 description 80
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 73
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 66
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 62
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
239000011541 reaction mixture Substances 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
239000012044 organic layer Substances 0.000 description 32
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 32
229910052943 magnesium sulfate Inorganic materials 0.000 description 30
235000019341 magnesium sulphate Nutrition 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000000843 powder Substances 0.000 description 23
239000012267 brine Substances 0.000 description 22
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 21
229930016911 cinnamic acid Natural products 0.000 description 21
235000013985 cinnamic acid Nutrition 0.000 description 21
239000005457 ice water Substances 0.000 description 21
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
239000002244 precipitate Substances 0.000 description 19
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 18
239000000725 suspension Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000013078 crystal Substances 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
238000001914 filtration Methods 0.000 description 16
238000001816 cooling Methods 0.000 description 15
239000003921 oil Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
238000012746 preparative thin layer chromatography Methods 0.000 description 13
239000007787 solid Substances 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
WORJEOGGNQDSOE-ASTXPPQBSA-N trichloro(deuterio)methane;trideuterio(deuteriooxy)methane Chemical compound [2H]C(Cl)(Cl)Cl.[2H]OC([2H])([2H])[2H] WORJEOGGNQDSOE-ASTXPPQBSA-N 0.000 description 12
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
229940114081 cinnamate Drugs 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000003828 vacuum filtration Methods 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
HAIBKCNQUDXDHR-UHFFFAOYSA-N 2-amino-n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-n-methylacetamide Chemical compound NCC(=O)N(C)C1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1Cl HAIBKCNQUDXDHR-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 9
238000003818 flash chromatography Methods 0.000 description 9
SMUQFGGVLNAIOZ-UHFFFAOYSA-N methylquinoline Natural products C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
150000008065 acid anhydrides Chemical class 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000002391 heterocyclic compounds Chemical class 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
239000012528 membrane Substances 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
239000003152 bradykinin antagonist Substances 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
NRPMBSHHBFFYBF-VMPITWQZSA-N ethyl (e)-3-(4-aminophenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=C(N)C=C1 NRPMBSHHBFFYBF-VMPITWQZSA-N 0.000 description 5
CDEIESVXIPSGGU-UHFFFAOYSA-N ethyl 3-(4-acetamidophenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(NC(C)=O)C=C1 CDEIESVXIPSGGU-UHFFFAOYSA-N 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
239000011630 iodine Substances 0.000 description 5
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 4
241000744472 Cinna Species 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
208000002193 Pain Diseases 0.000 description 4
125000004423 acyloxy group Chemical group 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
239000000872 buffer Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
JFGHUBKUQWGYES-UHFFFAOYSA-N n-[2,4-dichloro-3-[(2-methylquinolin-8-yl)oxymethyl]phenyl]-2-(1,3-dioxoisoindol-2-yl)acetamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC(=O)NC1=C(Cl)C(COC2=CC=CC3=CC=C(N=C32)C)=C(Cl)C=C1 JFGHUBKUQWGYES-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
MAMDZKZXIGHWCS-UHFFFAOYSA-N 2-Methyl-4-methoxychinolin Natural products C1=CC=C2C(OC)=CC(C)=NC2=C1 MAMDZKZXIGHWCS-UHFFFAOYSA-N 0.000 description 3
XFPKCKBFLNCGLD-UHFFFAOYSA-N 2-[n-acetyl-4-[3-[[2-[2,4-dichloro-n-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]amino]-3-oxoprop-1-enyl]anilino]acetic acid Chemical compound C=1C=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C(Cl)C=1N(C)C(=O)CNC(=O)C=CC1=CC=C(N(CC(O)=O)C(C)=O)C=C1 XFPKCKBFLNCGLD-UHFFFAOYSA-N 0.000 description 3
125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 3
XZERMVBWFJENLS-UHFFFAOYSA-N 4-[3-[[2-[2,4-dichloro-n-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]amino]-3-oxoprop-1-enyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C=CC(=O)NCC(=O)N(C)C1=CC=C(Cl)C(COC=2C3=NC(C)=CC=C3C=CC=2)=C1Cl XZERMVBWFJENLS-UHFFFAOYSA-N 0.000 description 3
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CZFLTXRVQCGSPW-UHFFFAOYSA-N ethyl 3-[4-(pyridin-2-ylmethoxy)phenyl]prop-2-enoate Chemical compound C1=CC(C=CC(=O)OCC)=CC=C1OCC1=CC=CC=N1 CZFLTXRVQCGSPW-UHFFFAOYSA-N 0.000 description 1
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VHDSSNNPEIXTLA-UHFFFAOYSA-N ethyl 3-[4-[(2-methoxyacetyl)-(pyridin-3-ylmethyl)amino]phenyl]prop-2-enoate Chemical compound C1=CC(C=CC(=O)OCC)=CC=C1N(C(=O)COC)CC1=CC=CN=C1 VHDSSNNPEIXTLA-UHFFFAOYSA-N 0.000 description 1
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